How to send my boyfriend soft, frosted sugar cookies for Valentine’s Day?
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My boyfriend and I live 4 hours apart. Same state. We won’t see each other on Valentine’s Day and I wanted to send him some frosted sugar cookies that I made. However, I heard you shouldn’t ship soft sugar cookies that are have toppings (such as icing/frosting). Is this possible so the cookies won’t get ruined?
I planned on putting them on top of a piece of bread (to keep them soft) in a tupperware container. I just don’t want them to get ruined in the mail and I want them to stay soft and fresh.
And when should I ship them? Valentine’s Day is on a Monday and I’d pay the extra to get fast shipping but since there’s no shipping on Sunday, idk what to do 
use a big Tupperware container. but in the layers of cookies put parchment paper in-between
you could call a bakery in the city he is in and order some cookies to be delivered to him. That way you will be certain they will arrive to him in perfect shape.
I work at a bakery and we take orders like that all the time from folks as far away as in a different country.
The key to shipping cookies so that they arrive in the condition you want is to wrap them very carefully, box them, then put them in a shipping carton with enough bubble wrap to keep the box of cookies suspended in the middle of the box.
I think you are on the right track with a cardboard bottom. I would then place a piece of wax paper cut the same size as the cardboard, gently on top of the iced cookie. Then I would slide the cookie into a zip-top bag. Once the cookie was in the bag, I would add a quarter of a slice of bread under the cardboard. The bread will ensure the cookie stays fresh and moist. (You can use 1 slice of bread for 4 cookies).
Once the cookies are bagged, put them in a box padded with bubble wrap, and put the cookies inside in a single layer. If you need to put another layer on top, make sure you pad with more bubble wrap. Top the cookies with more bubble wrap. To test that they won’t move, close the box (but do not seal) and shake the box back and forth. If you hear anything moving, add more bubble wrap, or fill in holes with newsprint.
Seal the box, then line a larger shipping carton with lots of bubble wrap, on the bottom and along the sides and leave room for more on top of your box. The idea is to “float” your box of cookies in the center of the shipping carton so that it does not move or get damaged.
Seal the shipping carton after testing for any movement the way you did for the cookie box
This may seem like a lot of work and supplies, but it is the only way I’ve ever had any success shipping cookies that arrived undamaged and infinitely fresh.